5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE Chemical Properties

Melting point:

217.9-218.2 °C

Boiling point:

344.8±44.0 °C(Predicted)

Density 

1.476±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-3.48±0.20(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C9H6ClNO3/c1-11-6-4-2-3-5(10)7(6)8(12)14-9(11)13/h2-4H,1H3

InChIKey

BTNWNXWHFWYONH-UHFFFAOYSA-N

SMILES

N1(C)C2=CC=CC(Cl)=C2C(=O)OC1=O

5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-diones from 5-chloro-1H-benzo[d][1,3]oxazine-2,4-diones and iodomethane: Iodomethane (2 mL, 4.6 mmol, 4 equiv) and N,N-diisopropylethylamine (DIPEA, 1 mL, 0.74 mol) were suspended at room temperature in N,N-dimethylacetamide (DMA, 10 mL) and stirred for 10 min. Subsequently, 5-chloroisatoic anhydride (200 mg, 1.01 mmol, 1 eq.) was added and the reaction mixture was stirred at 40 °C for 5 hours. Upon completion of the reaction, the resulting product 5-chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione was collected by filtration and washed with distilled water to give the pure product (150 mg, 70% yield). The melting point of the product was 224 °C. Infrared spectra (KBr) showed characteristic absorption peaks υ1774, 1716, 1593 cm^-1. 1H NMR (DMSO-d6, 300 MHz) δ 7.78 (t, J = 8.1 Hz, 1H), 7.42 (m, 2H), 3.45 (s, 3H). Elemental analysis results: calculated values for C9H6ClNO3: C, 51.08; H, 2.86; Cl, 16.75; N, 6.62; O, 22.68. measured values: C, 51.12; H, 2.36; Cl, 16.71; N, 6.58.

References

[1] Organic Process Research and Development, 2007, vol. 11, # 4, p. 674 - 680
[2] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 2, p. 437 - 440
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 1 - 10
[4] Monatshefte fur Chemie, 2016, vol. 147, # 6, p. 1069 - 1079
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088

5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE(40707-01-5)Related Product Information

• 5-Chloro-[1,2,4]triazolo[1,5-a]pyridine
• 5-CHLORO-3-HYDROXY (1H)INDAZOLE
• 5-CHLORO-1H-INDOL-3-METHYLAMINE
• 5-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid
• 5-Chloro-1,3,4-thiadiazol-2-ylamine
• 6-Chloro-3H-1,2,3-triazolo[4,5-c]pyridine
• 5-CHLORO-1H-PYRROLO[2,3-C]PYRIDINE
• Isatoic Anhydride
• Methyl 2-(methylamino)benzoate
• 3-CHLORO-N,N-DIMETHYLANILINE
• 2-Amino-6-chlorobenzoic acid
• 2-DIMETHYLAMINOBENZOIC ACID
• N-methylisatoic anhydride
• Methyl 2-chlorobenzoate
• 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE
• 5-CHLORO-3,1-BENZOXAZIN-2,4-DIONE
• 1,4-dihydro-2H-3,1-benzoxazin-2-one
• (2-AMINO-6-CHLORO-PHENYL)-METHANOL